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Gil Gunderson (usually referred to as Ol' Gil or Gil) is an unsuccessful and unlucky businessman of Springfield.

Gil has held many different jobs, all of which he eventually quits because something bad happens to him: For example, being shot in his first day as a bank security guard.

Gil frequently refers to himself in the third person ("C'mon, help ol' Gil out here!"). He has a tendency to punch people violently in the arm while trying to tell a story. Gil has been married, as evidenced by his mentioning that his wife was going to leave him if he didn't start "bringing in the green". Later, when he telephoned his wife and overheard her carousing with his friend, he didn't have the heart to stop her.

He has several health problems, including bronchitis and a bad back. He's also a strong moocher, and is adept at piano singalongs.

Among the large number of jobs Gil has had is real estate agent. When Marge started working as a realtor, Lionel Hutz told her, "Welcome to the big league, Marge. There's over fifty years of experience right in this room! And forty-two of those years are Gil's!", which seemed to imply that before he ran into Marge, Gil actually kept professions. He used to be a salesman, but he didn't sell any cars. He was almost going to sell one to Homer, but another salesman took his sale...